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Learning the Long Lesson.
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“So Twilight,” You began. You had just fulfilled your promise to finger the purple pony into a quivering mess. She had chastised you a little bit as she had wanted to at least do it in the living room, as part of your practice but the verbal lashing was short. She didn’t have much energy for it, after what you did. “Why is masturbation such a big deal? I’ve never seen those looks you guys were giving me on a pony before.”
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She winced at the ‘M’ word. “I sometimes forget that you’re not privy to all of our culture. You fit in so well..” She trailed off a bit toward the end. You ran your fingers through her mane, she let out a long sigh and removed your hand as she sat up. “As far as we know, ponies have always given relief to one another. It goes back as far as written history, even some hieroglyphs in old tombs and caves depict ponies reliving each other. It’s a natural thing.”
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“Yeah. I mean, I kind of get that now. But..”
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“..Well, um. When somepony does.. That. It means they’ve resigned themselves to not be friendly with anypony. They won’t help anyone, and won’t allow anypony to help them, ever. It’s a vicious thing to imply, an open letter of dispassionate disgust or even hate.”
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Only in a world of talking horses could having a wank ever be ubiquitous with turning your back on society. It only makes sense that they all were so worried about you. Even now, with Twilight looking down at you, a glimpse at that hurt still lingered. You pulled her into a hug.
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“You know I don’t hate you, right?”
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“Of course, Anon.” She patted a hoof against your back. “But you still have to finish your lessons.”
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You chuckled. You weren’t trying to squirm out of your lessons, but you had a feeling she mentioned that for a reason. “What’s next on the agenda then?”
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“It’s Applejack’s turn tomorrow,” She yawned, and lay down. “You might want to get some sleep. She’s very spartan with her training. You’ll need your energy.”
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You lie down next to the book horse and close your eyes. She’s facing you and you’re facing the ceiling. The rhythm of her breathing in your left ear slowly dulls your senses and lulls you into a gentle sleep.
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You are still Anonymous and you barely remember the definition of the words “gentle sleep” anymore. Applejack arrived early the morning after Twilight’s lesson. How early? The sun wasn’t up yet, the dew still lay heavy on the foliage, and it was still bitter cold. After a short conversation with Twilight, Applejack ‘updated’ your lesson a bit. You were now having a brisk walk to Applejack’s house, in your underwear.
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“Twi told me ya’ll were shy about yer body, I figured we could squeeze a little practice in now,” The cold making every word accompany a billow of vapor from the orange mare’s muzzle. “yer proper lesson won’t begin until noon, but I need to get a head start on today’s work if I’m going ta spent all afternoon teaching ya some manners!”
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You tried to ignore the stares the early risers were giving you on your way out of town. You always knew some ponies were undressing you with their eyes before, now it looks like they’d have to do a lot less work. One pony even stopped her jog and started walking backward to ogle you for just that bit longer.
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The sun had been risen properly by the time you made it to the Apple house. It was literally a barn. Surprisingly, there were more than apples being grown here. From a glance, you could make out corn, what looked like carrots, and lettuce. Livestock was also present.
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Applejack took you into her home and sat you on the couch. “You stay put while I finish up the rest of my work, ya hear? Get some rest if ya can, when I come back in, we’ll start your lesson.” With that, she left you in her living room, in your skivvies.
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Luckily for you, none of the rest of the Apple family were awake to see you almost naked in their living room. You knew that ponies were almost always naked and rarity used to love to tease you about your clothes. That was until you pointed out that ponies bits were usually hidden behind their tail for modesty’s sake while yours would be at eye level to everypony you met, and that she’d likely be uncomfortable if she was forced into walking backwards with her tail tied to her back.
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You were too uncomfortable to get any more rest. Applejack came back inside a few hours later to find you looking through a hoof-written cookbook that had happened to be on a table near the window. It had gotten considerably warmer since she left, it was almost hot out. Applejack had rivulets of sweat on her coat. Clearly she had been working hard.
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“C’mon there big feller,” she sounded almost out of breath. “Time to teach ya a thing or two.”
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She took out just outside earshot of the house into a clearing. Much to your surprise, there were two ponies already there. Big mac greeted you with a nod, Cheerilee gave you a blushing ‘hello’. Clearly she hadn’t been told you were going to be in your underpants.
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“I’ve been talking ta Pinkie a bit since yesterday about just what I should do with ya,” she began after you were seated. “She told me that watching other ponies get relived gets ya a little hot under the bridle. She also told me ya’ll were taking yer sweet time in acting on yer own initiative.” She gestured towards her guests. “So here’s what’s gonna happen..”
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You gulped. You had assumed that Applejack was the brawn of the group, but her ‘lesson’ was downright meticulous and diabolical.
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“Cheerilee is going to pretend to need relief, and Big Mac is going to give it to her. You’ll have ta talk to Cheerilee during, and I’ll be right here,” she had said before placing her head on your thigh. You were sitting with your legs under you and her head was right next to your equipment. “And if at any point you get riled up, I’ll be able to see it, smell it too I recon and then I’ll need some relief that you WILL provide.” Her tail twitched as she said this. “Not with yer hand thingies neither.”
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You met her green eyes briefly as Big Mac mounted Cheerilee. Cheerilee seemed to be having a fair amount of fun, considering. You concluded that as a teacher, this must seem like a private sex-ed lesson or something similar. You hoped anyway.
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“So hey,” you began. You regretted this immediately as Big Mac entered her at precisely that moment.
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She closed her eyes and let a low groan escape from her nostrils, keeping her mouth closed. It didn’t last, her eyes were open again before you knew it and she looked at you and Applejack as if you had just bumped into each other at the park.
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“W-what’s it like being a teacher in a small town like Ponyville?” you asked. Wet shloping sounds were starting to issue from the couple in front of you as Big Mac pistoned back and forth, his face as neutral as ever. You tried to stare squarely in Cheerilee’s eyes, hoping beyond hope that some kind of tunnel vision would make you forget about Cheerilee’s backside being brazenly pounded.
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“I cherish the fact that Ponyville’s population isn’t that high actually. I only teach one class of students currently, at the most it’s been two. It really allows me to fine tune my classes to make sure nopony gets left left behind,” She said cheerfully, moaning slightly every few words.
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You could literally hear Big Mac’s balls slapping against her. Despite yourself you glanced downward and saw a veritable flood of mare slime running down Cheerilee’s back leg. You even saw some of it ooze downward in a thick slimy drip right between her legs. You felt man-meat give a definite twitch.
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You were about to ask if she’d considered moving to a bigger city, but Big Mac spoke first.
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“Where d’ya want it?”
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Cheerilee had seemingly zoned out a little staring at you. It was with a start that she replied, “Oh! Um, how about on my teats?” She stepped forward, sliding Big Mac out of her with a wholly unnecessary sound like removing a whole frozen turkey from a bowl of wet jello and beans. She then proceeded to roll over on her back with her hind legs splayed wide and her front legs tucked in. She stared at you the whole time.
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Big Mac took Cheerilee’s hind legs and pressed them together with his front legs. He then pressed his tool through her thighs. Cheerilee was giving you a smile, when the tip of Big Mac’s cock flared. He gave a grunt, and his first shot of horse cream hit Cheerilee in the chin, and ended up coating some of her face. He used his hoof to push it downward for the second shot onward. Covering her perky teats with shot after shot of musky horse seed.
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You’d obviously failed to maintain your modestly. You’d failed around the time the thighjob started. Applejack had given you a small cough and a smug grin. If you didn’t expect better from the element of honesty, you’d say the test was rigged.
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Your boxers were only barely concealing your member. The length and shape of it were pretty well defined through the fabric. The tip had darkened with the pre you inadvertently (as with all pre) loosed. You looked back down at Applejack who was looking back at you.
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Let it be said that you were never one to back down from a challenge. Let it also be said that no human on earth has ever been more embarrassed than you are at this moment. You were buck naked in front of three ponies. Applejack nose to tip with your trouser snake.
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“That there’s a fine piece of work ya got Anon. Shame to keep it all caged up all day.” She gave it a big sniff that made you want to die. “Smells mighty fine, like a stallion among stallions.” She cleared her throat. “Well, I suppose ya’ll know what’s coming next?”
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You could only guess that she was talking only to you, because Big Mac and Cheerilee were chatting among themselves. “You wanted me to uh, relieve you. Right?” No hands though, she probably wanted you to eat her out. You suppose that’s only the natural next step from fingering.
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“Yep! You’re gonna put her stallionhood in me.”
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“Woah, woah, woah!” You exclaimed. “I already told Rainbow Dash I’d-”
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She stomped her front hoof. “Consarn it, I know that! Well? think it through ya dummy. If ya used yer fingers, or even yer mouth, I’d still have ta relieve ya, and don’t you go saying I don’t. Look at the state yer in.” She pointed her hoof at your still throbbing erection. “I can’t use my mouth to do it fer Pinkie’s sake, and I ain’t using my hooves, I’ve been working since the stars were still out, to be frank they’re aching something awful. So, if I can’t use my mouth, and the main road’s closed, yer gonna have to take the back road.”
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She rolled her haunches and turned around slowly. She then flipped her tail up. Her marehood was glistening in the sunlight, winking occasionally. Due north was her plump orange ring of a ponut. It gave a few twitches while you stared.
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“Well? I won’t force ya, but I don’t recon yer the type of stallion to leave a mare in need.”
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Diabolical. She knew exactly what buttons to push. This wasn’t like the lessions with Rarity or Twilight, Applejack was indeed as spartan as Twilight said she was. She was playing on your sense of decency in order to push you out of your comfort zone.
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You stepped forward. It wasn’t so bad really, at least the other two were distracted. Applejack’s rear was an amazing sight as well, she was toned and plump in all right right places. You swallowed. You were going to do this, and if you were going to do this, you were going to do it right.
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You got down on your knees, Applejack’s ass directly in your face. You start kneading those buns, earning a sigh from the farm mare. You exhale, then press your face between her cheeks. It doesn’t take long for you to find your mark, you give Applejack’s tailhole a wide lick, it twitches under your tongue. She nearly jumps.
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“Ya could have just licked yer fingers..” She began.
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You didn’t reply, instead you began licking her backdoor again. Again and again you gave her puckered anus long wet licks. From the way she was starting to moan and squirm, she was clearly enjoying it more than she though she would. You slowly slid your tongue inside her puckered doughnut, you pressed your lips around it to get your tongue in that much deeper.
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Applejack couldn’t help but let out a loud throaty moan at this. “Woah nelly, you’ve got a talent for that romeo.” She moan lightly as your slid your tongue out. Her asshole now dripping with your spit.
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You took two fingers an dipped them in her absolutely sodden sex. She was easily twice as wet as Cheerilee was earlier. You smeared her mare juice over your turgid tool. You then sat on your butt, legs wide as you guided Applejack’s plump posterior down onto your tool. “Have a seat Applejack, rest your hooves.”
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“Now yer getting it!” She said as she slowly slid her tight hole over your hardness. “It’s just giving somepony a helping hoof, nothing ta be scared of.”
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And something kind of clicked as you watched your dick disappear inside a horse’s asshole. She seemed to be just as relieved to be taking your cock as she did to finally be off her hooves after a hard day’s work. Sex was just a solid on pony did for another, like helping someone with heavy groceries or helping someone get a boost on their car battery because you happened to have some jumper cables.
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You started to move. Applejack’s insides were hot and tight almost to the point of past endurance.
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Ponies started gathering into the clearing. More than you could count. From what you could remember, these were members of the apple family. You froze.
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“We’re here for the picnic Applejack!” A mare said. They appeared to be carrying all sorts of checkered and tartan sacks and boxes full of presumably apple related catering.
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“Apple Fritter, yer right on time.” Applejack said casually. Lay yet towels down anywhere ya want.
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The ponies began setting up their little areas. Apple Fritter lay her towel down next to you and Applejack. A few of the ponies greeted you. You had to shake yourself both physically and mentally to recall the epiphany you’d just had. Sure, a few ponies were looking directly at you, but most of them were talking to each other, catching up with one another and sharing treats. You replied to the greetings as casually as you could.
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Applejack started to move. She cooed softly as your member grew harder inside her as she slid you in and out of her derriere. Apple Fritter offered you both a delicious looking cherry glazed fritter. Applejack ate hers in one bite, a feat you’ve seen ponies do on occasion, while you asked if she could hold it for just a few more minutes.
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A few minutes being a generous estimate as Applejack took that as a challenge and decided to pick up the pace. Lewd sounds now emitting from Applejack’s ass caused only a couple ponies to give you a bemused glace then continue with their luncheon. They really didn’t care. Some of the ponies actually started to get some relief themselves.
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“It’s so nice to see you giving somepony a hand,” Apple Fritter said as she unpacked the rest of her picnic basket. “Some ponies in town were worried, but we apples knew you were just shy. Speaking of shy, Applejack did you know that Fluttershy w-”
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Applejack did not stop for that entire exchange, her ass seemed to be sucking you in as she pulled out and embracing you when she plunged it back in. You couldn’t take anymore. You gripped her hips and thrust into her. You could feel your urethra struggle to push back her ring enough to let your heavy load through. You almost shudder at the though of what would happen if she pinched her asshole closed around you right now. You shot your thick seed deep inside the orange farm horse, your back arched and your toes curled. You had never cum like this before. Applejack moaned and a gush of mare juice coated your lap as she reached orgasm.
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When you had finished, Applejack turned around. “Anon, you were one heck of a ride. But I do have to take points off. It’s rude for a stallion to finish without asking the mare where she prefers it.” She pulled herself off of you with a similar sound to Cheerilee earlier, only with a faint ‘pop’ when your tip left her anus. “This is going to be leaking out of me all day,” she said as she gave her slightly gaping asshole a flex and a twitch. “Apple Fritter, you mind helping me out with this?”
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“Oh wow, I get to taste Anon’s cum?! Count me in!” Casually as you like, she trots over to Applejack and begins to lick your load out of her ass with loud slurping sounds. You can actually hear her swallowing it. You feel yourself slowly get hard again at the sight.
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Applejack sees this from the corner of her eye. “Looks like you’re ready for another ride partner.” You see her marehood wink under Apple Fritter’s chin. Apple Fritter gives that a long sucking too. Looks like this is going to be a particularly long lesson.
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3167 17.07 KB 127
by Deandingus